CA2070754C - Pyrolysis of naturally occurring cresylic acid mixtures - Google Patents
Pyrolysis of naturally occurring cresylic acid mixtures Download PDFInfo
- Publication number
- CA2070754C CA2070754C CA002070754A CA2070754A CA2070754C CA 2070754 C CA2070754 C CA 2070754C CA 002070754 A CA002070754 A CA 002070754A CA 2070754 A CA2070754 A CA 2070754A CA 2070754 C CA2070754 C CA 2070754C
- Authority
- CA
- Canada
- Prior art keywords
- cresylic acid
- guaiacol
- pyrolysis
- stream
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 238000000197 pyrolysis Methods 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims abstract description 160
- 238000000034 method Methods 0.000 claims abstract description 34
- 230000008569 process Effects 0.000 claims abstract description 29
- 229960001867 guaiacol Drugs 0.000 claims description 78
- 239000000047 product Substances 0.000 claims description 33
- 230000015572 biosynthetic process Effects 0.000 claims description 29
- 239000000571 coke Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 23
- 239000006227 byproduct Substances 0.000 claims description 19
- 238000010791 quenching Methods 0.000 claims description 18
- 229910001220 stainless steel Inorganic materials 0.000 claims description 11
- 239000010935 stainless steel Substances 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 238000012856 packing Methods 0.000 claims description 5
- 230000000171 quenching effect Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 230000008016 vaporization Effects 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000006200 vaporizer Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000003245 coal Substances 0.000 description 16
- 239000003077 lignite Substances 0.000 description 16
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 13
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 11
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229940100630 metacresol Drugs 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- 239000004576 sand Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000007701 flash-distillation Methods 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- -1 agrichemical Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- 229910001203 Alloy 20 Inorganic materials 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 150000003739 xylenols Chemical class 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical class CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- WBHAUHHMPXBZCQ-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class COC1=CC=CC(C)=C1O WBHAUHHMPXBZCQ-UHFFFAOYSA-N 0.000 description 1
- OMNGOGILVBLKAS-UHFFFAOYSA-N 2-methoxyphenol Chemical compound COC1=CC=CC=C1O.COC1=CC=CC=C1O OMNGOGILVBLKAS-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000061 acid fraction Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052614 beryl Inorganic materials 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000013462 industrial intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000003498 natural gas condensate Substances 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
- C07C39/07—Alkylated phenols containing only methyl groups, e.g. cresols, xylenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/743,077 US5146010A (en) | 1991-08-09 | 1991-08-09 | Pyrolysis of naturally occurring cresylic acid mixtures |
| US743,077 | 1991-08-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2070754A1 CA2070754A1 (en) | 1993-02-10 |
| CA2070754C true CA2070754C (en) | 2002-02-26 |
Family
ID=24987429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002070754A Expired - Lifetime CA2070754C (en) | 1991-08-09 | 1992-06-09 | Pyrolysis of naturally occurring cresylic acid mixtures |
Country Status (19)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5254750A (en) * | 1993-04-05 | 1993-10-19 | Merichem Company | Removal of guaiacol from cresylic acid by heating with a strong base |
| KR20040019145A (ko) * | 2002-08-26 | 2004-03-05 | 주식회사 이코바이오 | 천연 구강청정제 조성물 |
| JP5892277B2 (ja) * | 2012-11-30 | 2016-03-23 | トヨタ自動車株式会社 | グアヤコールを主成分として含む混合物の、液相中での脱メチル化又は脱メトキシ化反応用触媒、及びこれを用いたフェノール又はカテコールの製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE204474C (enrdf_load_stackoverflow) * | ||||
| US3375283A (en) * | 1965-07-29 | 1968-03-26 | Crown Zellerbach Corp | Preparation of methoxy phenols from spent pulping liquors |
| US4208350A (en) * | 1978-03-06 | 1980-06-17 | Boise Cascade Corporation | Separating phenols from alkaline pulping spent liquors |
| US4420642A (en) * | 1982-02-18 | 1983-12-13 | Fmc Corporation | Selective removal and recovery of catechol mixed with 2-methallyloxyphenol |
| SU1235860A1 (ru) * | 1984-12-10 | 1986-06-07 | Институт горючих ископаемых | Способ получени фенола и изопропилбензола |
| JPS6479127A (en) * | 1987-09-21 | 1989-03-24 | Jgc Corp | Production of phenols from lignin |
-
1991
- 1991-08-09 US US07/743,077 patent/US5146010A/en not_active Expired - Lifetime
-
1992
- 1992-06-09 CA CA002070754A patent/CA2070754C/en not_active Expired - Lifetime
- 1992-06-09 GB GB9212141A patent/GB2258463B/en not_active Expired - Lifetime
- 1992-06-15 ZA ZA924361A patent/ZA924361B/xx unknown
- 1992-06-30 TW TW081105187A patent/TW204338B/zh not_active IP Right Cessation
- 1992-07-01 DE DE4221598A patent/DE4221598A1/de not_active Withdrawn
- 1992-07-01 JP JP17455592A patent/JP3190433B2/ja not_active Expired - Lifetime
- 1992-07-01 FR FR9208094A patent/FR2680170B1/fr not_active Expired - Lifetime
- 1992-07-09 CZ CZ94256A patent/CZ282619B6/cs not_active IP Right Cessation
- 1992-07-09 ES ES92914678T patent/ES2090665T3/es not_active Expired - Lifetime
- 1992-07-09 AT AT92914678T patent/ATE138632T1/de not_active IP Right Cessation
- 1992-07-09 KR KR1019940700441A patent/KR940702151A/ko active Granted
- 1992-07-09 AU AU23106/92A patent/AU662754B2/en not_active Expired
- 1992-07-09 GE GEAP19922689A patent/GEP19991789B/en unknown
- 1992-07-09 EP EP92914678A patent/EP0597882B1/en not_active Expired - Lifetime
- 1992-07-09 DE DE69211138T patent/DE69211138T2/de not_active Expired - Lifetime
- 1992-07-09 PL PL92302349A patent/PL169132B1/pl unknown
- 1992-07-09 WO PCT/US1992/005763 patent/WO1993002996A1/en active IP Right Grant
- 1992-07-09 KR KR1019940700441A patent/KR0144110B1/ko not_active Expired - Lifetime
- 1992-07-09 SK SK141-94A patent/SK280080B6/sk not_active IP Right Cessation
- 1992-07-09 UA UA94005296A patent/UA37193C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0597882B1 (en) | 1996-05-29 |
| TW204338B (enrdf_load_stackoverflow) | 1993-04-21 |
| PL169132B1 (pl) | 1996-06-28 |
| DE69211138D1 (de) | 1996-07-04 |
| ES2090665T3 (es) | 1996-10-16 |
| WO1993002996A1 (en) | 1993-02-18 |
| GB9212141D0 (en) | 1992-07-22 |
| UA37193C2 (uk) | 2001-05-15 |
| GB2258463B (en) | 1995-04-05 |
| DE69211138T2 (de) | 1997-01-23 |
| JPH05201901A (ja) | 1993-08-10 |
| KR940702151A (ko) | 1994-07-28 |
| FR2680170B1 (fr) | 1994-10-07 |
| DE4221598A1 (de) | 1993-02-18 |
| CA2070754A1 (en) | 1993-02-10 |
| US5146010A (en) | 1992-09-08 |
| EP0597882A1 (en) | 1994-05-25 |
| CZ282619B6 (cs) | 1997-08-13 |
| AU2310692A (en) | 1993-03-02 |
| ATE138632T1 (de) | 1996-06-15 |
| CZ25694A3 (en) | 1994-05-18 |
| GB2258463A (en) | 1993-02-10 |
| AU662754B2 (en) | 1995-09-14 |
| GEP19991789B (en) | 1999-10-05 |
| JP3190433B2 (ja) | 2001-07-23 |
| SK14194A3 (en) | 1994-09-07 |
| ZA924361B (en) | 1993-08-17 |
| FR2680170A1 (fr) | 1993-02-12 |
| KR0144110B1 (ko) | 1998-07-15 |
| SK280080B6 (sk) | 1999-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |